Find Annamycin manufacturers, exporters & distributors on PharmaCompass

Annamycin

Annamycin

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

1 NDC API

1 NDC API

DEVELOPMENTS

26 Drug(s) in Development

26 Drug(s) in Development

DIGITAL CONTENT

26 News

26 News

Product Search

API SUPPLIERS

API Suppliers

US DMFs Filed

CEP/COS Certifications

JDMFs Filed

Other Certificates

Other Suppliers

API REF. PRICE (USD / KG)

API Market Place

INTERMEDIATES

DOSSIERS // FDF

USA (Orange Book)

Europe

Canada

Australia

South Africa

Uploaded Dossiers

GLOBAL SALES (USD Million)

U.S. Medicaid

Annual Reports

FDF Market Place

EXCIPIENTS

PATENTS & EXCLUSIVITIES

USFDA Orange Book Patents

USFDA Exclusivities

DIGITAL CONTENT

Blog #PharmaFlow

News

REF STANDARD

EDQM

USP

Other Listed Suppliers

SERVICES

Also known as: 92689-49-1, 2'-iodo-3'-hydroxy-4'-epi-4-demethoxydoxorubicin, Snu299m83q, (7s,9s)-7-(((2r,3r,4r,5r,6s)-4,5-dihydroxy-3-iodo-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7,8,9,10-tetrahydrotetracene-5,12-dione, 5,12-naphthacenedione, 7-((2,6-dideoxy-2-iodo-alpha-l-mannopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxyacetyl)-, (7s-cis)-, Unii-snu299m83q

Molecular Formula

C₂₆H₂₅IO₁₁

Molecular Weight

640.4 g/mol

InChI Key

CIDNKDMVSINJCG-GKXONYSUSA-N

FDA UNII

SNU299M83Q

Annamycin is a lipophilic, anthracycline antineoplastic antibiotic. Annamycin intercalates into DNA and inhibits topoisomerase II, thereby inhibiting DNA replication and repair as well as inhibiting RNA and protein synthesis. This agent appears to not be a substrate for the p-glycoprotein associated multidrug-resistance (MDR) transporter; therefore, overcoming the resistance pattern seen with other anthracycline compounds.

1 2D Structure

Annamycin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(7S,9S)-7-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-3-iodo-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7H-tetracene-5,12-dione

2.1.2 InChI

InChI=1S/C26H25IO11/c1-9-19(30)24(35)18(27)25(37-9)38-13-7-26(36,14(29)8-28)6-12-15(13)23(34)17-16(22(12)33)20(31)10-4-2-3-5-11(10)21(17)32/h2-5,9,13,18-19,24-25,28,30,33-36H,6-8H2,1H3/t9-,13-,18+,19-,24-,25-,26-/m0/s1

2.1.3 InChI Key

CIDNKDMVSINJCG-GKXONYSUSA-N

2.1.4 Canonical SMILES

CC1C(C(C(C(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)CO)O)I)O)O

2.1.5 Isomeric SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)CO)O)I)O)O

2.2 Other Identifiers

2.2.1 UNII

SNU299M83Q

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2'-iodo-3'-hydroxy-4'-epi-4-demethoxydoxorubicin

2.3.2 Depositor-Supplied Synonyms

1. 92689-49-1

2. 2'-iodo-3'-hydroxy-4'-epi-4-demethoxydoxorubicin

3. Snu299m83q

4. (7s,9s)-7-(((2r,3r,4r,5r,6s)-4,5-dihydroxy-3-iodo-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7,8,9,10-tetrahydrotetracene-5,12-dione

5. 5,12-naphthacenedione, 7-((2,6-dideoxy-2-iodo-alpha-l-mannopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxyacetyl)-, (7s-cis)-

6. Unii-snu299m83q

7. Ar-522

8. (7s,9s)-7-[(2r,3r,4r,5r,6s)-4,5-dihydroxy-3-iodo-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7h-tetracene-5,12-dione

9. Schembl19368

10. Dtxsid901027238

11. Zinc3918134

12. Db06420

13. 689a491

14. Q4767903

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₅IO₁₁
Molecular Weight	640.4 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	4
Exact Mass	640.04416 g/mol
Monoisotopic Mass	640.04416 g/mol
Topological Polar Surface Area	191 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	962
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in breast cancer and leukemia (unspecified).

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

5.2 Mechanism of Action

Annamycin belongs to the anthracycline class of drugs, and has a pleiotropic mechanism of action where it targets topoisomerase II, causing strand breaks in DNA. Annamycin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.